Progress toward the total synthesis of 9β-hydroxyvertine: Construction of an advanced quinolizidine intermediate

Authors

Thanaphat Thaima, University of WollongongFollow
Anthony C. Willis, Australian National University
Stephen G. Pyne, University of WollongongFollow

RIS ID

137944

Publication Details

Thaima, T., Willis, A. C. & Pyne, S. G. (2019). Progress toward the total synthesis of 9β-hydroxyvertine: Construction of an advanced quinolizidine intermediate. Tetrahedron, 75 (36), 130476-1-130476-24.

Abstract

Progress toward the total synthesis of 9β-hydroxyvertine 2 is described. Our approach involves a Petasis borono-Mannich reaction to assemble a key intermediate A, securing the correct configuration at H-9 and H-10 in the final targeted molecule. Subsequent formation of the quinolizidine framework B allowed the synthesis of an advanced intermediate containing all but the lactone moiety of 2. Our unsuccessful attempts at introducing this lactone feature are also described.

Grant Number

ARC/DP130101968